Application of the aza-Diels-Alder reaction in the synthesis of natural products
The Diels-Alder reaction that involves a nitrogen atom in the diene or dienophile is termed the aza-Diels-Alder reaction. As well as the powerful all-carbon Diels-Alder reaction, the aza-Diels-Alder reaction has also played an important role in the total synthesis of natural products. Herein, we rev...
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| Published in | Organic & biomolecular chemistry Vol. 15; no. 15; pp. 315 - 3129 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
England
11.04.2017
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| Subjects | |
| Online Access | Get full text |
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| Summary: | The Diels-Alder reaction that involves a nitrogen atom in the diene or dienophile is termed the aza-Diels-Alder reaction. As well as the powerful all-carbon Diels-Alder reaction, the aza-Diels-Alder reaction has also played an important role in the total synthesis of natural products. Herein, we review various natural products using an aza-Diels-Alder reaction as a key step to their total synthesis, and divide the syntheses into inter- and intra-molecular aza-Diels-Alder reactions and a retro-aza-Diels-Alder reaction. Inter- and intra-molecular aza-Diels-Alder reactions involve an imine as an electron deficient dienophile and an imine as an electron deficient azadiene. The significance of the aza-Diels-Alder reaction for the construction of a six-membered ring containing nitrogen is tremendous, but the development of asymmetric, in particular catalytic enantioselective intramolecular aza-Diels-Alder reaction in the total synthesis of natural products remains highly challenging, and will no doubt see enormous advances in the future.
The Diels-Alder reaction that involves a nitrogen atom in the diene or dienophile is termed the aza-Diels-Alder reaction. |
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| Bibliography: | Nicholas Green is currently a Ph.D. student at the Research School of Chemistry, the Australian National University (ANU). He pursued his Ph.B. (Science) at the ANU and received an Honours degree with the University Medal in 2011, taking up doctoral studies as a Rodney Rickards scholar soon after. His research interests include the use of highly unsaturated molecules in synthesis and the catalytic, enantioselective Diels-Alder reaction. Sheng-Zhen Xu graduated from the Central China Normal University and obtained his Ph.D. degree in 2007 under the supervision of Prof. Ming-Wu Ding and Prof. Wen-Jing Xiao. During the period from Aug. 2014 to Aug. 2015, he studied at the Research School of Chemistry, the Australian National University (ANU). He is currently an associate Professor at Huazhong Agricultural University in China. His current research interests cover the synthesis and application of natural products. Min-Hui Cao graduated from the Central China Normal University and obtained her Master's degree in 2003 and earned her Ph.D. degree in 2012 under the supervision of Prof. De-Jiang Ni. During the period from August 2014 to August 2015, she studied at the Research School of Chemistry, the Australian National University (ANU). She is currently an assoc. professor at Huazhong Agricultural University in China. Her current research field covers the synthesis and application of natural products. ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-3 content type line 23 ObjectType-Review-1 ObjectType-Article-1 ObjectType-Feature-2 |
| ISSN: | 1477-0520 1477-0539 |
| DOI: | 10.1039/c6ob02761j |